


Eileen Pegging Sam

by destielseason15



Category: Supernatural
Genre: Anal, Anal Fingering, Anal Play, Bottom Sam Winchester, F/M, Pegging, Strap-Ons, Top Eileen Leahy, Woman on Top, female on top
Language: English
Status: Completed
Published: 2020-03-18
Updated: 2020-03-18
Packaged: 2021-03-01 04:20:36
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 862
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23199241
Author URL: https://archiveofourown.org/users/destielseason15/pseuds/destielseason15
Summary: This is my first female/male fic, I wrote something short because I was unsure of what to write, I got the idea from Twitter also @destielseason15 about Eileen pegging Sam. Always thought Eileen was a top in canon, and Sam is definitely a switch.
Relationships: Eileen Leahy/Sam Winchester
Comments: 2
Kudos: 17





	Eileen Pegging Sam

"I made one of your favorite foods" Sam starts off with.

Eileen puts her hands flat with palms touching each other rubbing in each for cheese, she then puts her left hand flat with her right fingers forward to form the outline of an upside down cup moving her fingers to touching the base and moving her right hand upward signing the words cheese and cake.

Sam has a smile then says Nutella(chocolate hazelnut spread) with Oreo(chocolate with cream filling cookies) crust, Elieen loves all things chocolate it's her favorite and smiles back remembering memories of last week's chocolate chip pie. Last week Dean was in the bunker unlike this week's vampire hunt and they were joking if it was pie or not still Dean loved and ate a lot of it. Sam goes to the kitchen and grabs two slices for him and Eilleen, extra whip cream for Eileen. Eileen eats it then teasingly says "I have a special surprise waiting for you in bed."

Sam rushes to finish putting away the dishes, feeling excited in his his boxers as he walks to his bedroom he now shares with Eileen. Eileen is standing there in a sheer black strappy teddy, Sam stares thinking she looks amazing with all the straps hugging all her curves. She says to Sam to take all his clothes off. Sam happily obligates to it starting with his shoes and shirt. He slowly goes button by button on his classic dark green plaid not wearing any shirt underneath, Eileen starting in awe. 

After what seems like forever he takes off his jeans his red plaid boxer-briefs showing just enough skin but as soon as Eileen sees it couldn't focus on anything more except for the outline of Sam's cock in them. Most girls like grey sweatpants but plaid is hotter for her. It's beautiful but still not as much as what's in it she thinks as Sam tugs on the saxx waistband pulling them down.

Eileen turns from the side showing off her strapless strap on already inside her waiting for the other side to be in Sam. Eileen looks at the bed Sam already going to it without command. Lying on his back with a pillow behind his back partially sitting up he spreading his legs ready for Eileen. Eileen strokes Sam's cock once then putting lube on her fingers. She puts one finger in and moved it inside of Sam. Eileen can see Sam's mouth opening in a moan.

Eileen was unsure if Sam would like it at first but is now sure that it's one of the best decisions she made. She's played with Sam's hole a bit before but nothing more a rimjob during a blowjob. Eileen can see how much he likes it until she puts three fingers in. Eileen presses the tip against his hole. Sam is screaming to do it now begging for it. She slowly insterts the lube covered dildo into his stretched asshole. 

Sam cries out a bit his cheeks flushed red. It's slightly painful for him unsure if he should tell Eileen to stop but the joy outweighs the pain. It has a slight burn to it but that makes it all the better. He unsure if he should stop or keep going. He opens her mouth wondering what to say and out of it says "fast, faster, the fastest you can go"

She can see that he's saying faster and quickens the pace. Sam looks like he's about to finish so Eileen stops pulling l the way out putting her hand on Sam's cock feeling it throb. Eileen leans down her chest against his stomach. She forgets about how it vibrates. She picks up the remote from the bedside table and puts it all the way to maximum. 

She insterts it back into Sam with ease. He clenches down on it screaming. She sees how much he enjoys, although she it enjoys it very much herself. Her pleasure is mutiplied knowing how much Sam loves it, she enjoys it but he does even more. Sam can tell too how much Eileen loves it and Eileen's pleasure is helping him too. Eileen continues to thrust her hips rocking in and out of Sam.

Eileen puts her hand on his cock and the other hand on his inner sensitive thigh. Sam rolls his eyes back as he cums. Eileen peaks too both of them lost in the moment. Eileen slides out and Sam says "maybe we should do this again?"

Eileen says "I think think we might need a larger dildo next time?"

Sam replies "whatever you want" as Eileen grabs a wet towel from the bathroom cleaning off his cum. Eileen takes off the dildo and sits against his back as they both fall asleep. 

Eileen and Sam are both awaken by his alarm. Eileen is annoyed but Sam suggests they go for a run along the lake. Eileen helps Sam get dressed as she also gets dressed wearing one of Sam's plaid shirts as a jacket fitting oversized on her. They leave the bunker driving and runs along the lake seeing the sun rise.

**Author's Note:**

> This is my first female/male fic, I wrote something short because I was unsure of what to write, I got the idea from Twitter also @destielseason15 about Eileen pegging Sam. Always thought Eileen was a top in canon, and Sam is definitely a switch.


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